Phosphorus oxychloride → [2-Chloro(3-chlorophenyl)-6-quinazolinyl](4-methylphenyl)-methanone

HRID 1441471Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1441471
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18](=[O:26])[C:19]4[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=4)[CH:16]=3)[NH:11][C:10](=O)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.P(Cl)(Cl)([Cl:30])=O>>[Cl:30][C:10]1[N:9]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)=[O:26])[CH:16]=2)[N:11]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 686874324-(3-chlorophenyl)-6-(4-methylbenzoyl)-2(1H)-quinazolinone

Produkt 1

HCID 17976110[2-Chloro(3-chlorophenyl)-6-quinazolinyl](4-methylphenyl)-methanoneAusbeute 70 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of intermediate 22 (0.041 mol) in phosphoryl chloride (105 ml) was stirred at 100° C. for 4 hours then cooled. The solvent was evaporated. The residue was taken up DCM. The solvent was evaporated. The residue was taken up in DCM. The mixture was poured out into ice water, basified with K2CO3 10% and extracted. The organic layer was separated, washed with water, dried (MgSO4), filtered and the solvent was evaporated. The residue was crystallized from CH3CN. The precipitate was filtered off and dried, yielding 11.4 g (70%) of intermediate 23. The mother layer was evaporated and purified by column chromatography over silica gel (eluent: cyclohexane/EtOAc; 90/10; 15-40 μm). The pure fractions were collected and the solvent was evaporated, yielding 1.7 g (10.5%) of [2-chloro-4-(3-chlorophenyl)-6-quinazolinyl](4-methylphenyl)-methanone (intermediate 23), mp. 156° C.

Aufarbeitung

  1. temperaturethen cooled
  2. customThe solvent was evaporated
  3. customThe solvent was evaporated
  4. additionThe mixture was poured out into ice water
  5. extractionextracted
  6. customThe organic layer was separated
  7. washwashed with water
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customthe solvent was evaporated
  11. customThe residue was crystallized from CH3CN
  12. filtrationThe precipitate was filtered off
  13. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5a3a07c7053b479ab58261a93f90ba0c
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07655654B2

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